It's five in the morning and while most New Yorkers are in bed, Jessica Singleton is preparing to film Bill de Blasio getting out of his. She has invaded the de Blasio house with a film crew to capture the candidate's morning routine for a day-in-the-life video she came up with to fulfill a strategic imperative to tell New Yorkers who he is. This is May 2013, when now-Mayor de Blasio was running a distant third in his Democratic primary behind both Christine Quinn and Bill Thompson. It was a race that New Yorkers were already sick of but also transfixed by—a primary hadn't been taken seriously since Mayor Bloomberg took office three terms earlier. No one candidate had a mandate yet (they often found themselves polling behind undecideds) so the field was open, but also barbed. Anthony Weiner had gotten into the race as an attempt to rejoin politics after his very public fall from grace, Quinn was being painted as Bloomberg junior, and John Liu was fighting off allegations of fundraising misdeeds on more than one front. People weren't talking a lot about Bill de Blasio, hence the invasion.

"I said, 'We need to do a video. Let's make it beautiful and let's not make it about campaign promises but show people why he's fighting for the things he's fighting for—because it's part of who he is."

Singleton, a veteran of Obama's campaign in Pennsylvania, had been hired a few months prior as the campaign's digital director along with the other core team members. "It was me, Rebecca [Katz], and the campaign manager and the fundraiser. When they were building the campaign infrastructure they really prioritized digital," she told ELLE. "The campaign manager for de Blasio saw Jessie's work in Pennsylvania and brought her with him. He knew she was capable of so much more and just put her in charge of the whole thing," Rebecca Katz, special advisor to the mayor and press whisperer, said.

Coming on board the de Blasio team put Jessie in charge of creating the content across all digital platforms that would motivate people to engage with the campaign; of analyzing and targeting groups based off the data she collected; of working with everyone from parent bloggers to online activists to hipsters for de Blasio; and of introducing the Mayor to the likes of Reddit AMAs and Buzzfeed ("never had I ever defined 'listicle' for my boss"). But she still had one more job that was just as challenging: Soothing the nerves of New York's anxious techies.

The first time I met 28-year-old Singleton was months ago at a breakfast hosted by Yahoo! and Internet Week New York (where the Mayor would eventually unveil his tech agenda for the City). She had come to meet members of the New York tech community, which were still nervous about her new boss taking over for Mayor Bloomberg. One had the feeling that if she hadn't been thrown into the lions' den that morning, she'd at least been thrown into some habitat with an animal that would gnaw at her leg until she gave it what it wanted. But, despite being outnumbered and having to field questions on everything from the lack of Fios coverage in the city to how start-ups here would recruit and retain engineering talent in that face of tech giants moving in next door, she was not shaken. In fact, this wasn't the first time Singleton had had this conversation. "I went on a pro-active, self-guided tour of the New York tech community starting in March and that didn't really ever end. I tried to meet as many people in the community as I could and it wasn't really about building good will, it was about getting good ideas. The tech community just wants conditions [that are right for growth] and a City Hall that supports them."

She touts the tech-talent pipeline initiative that the administration has announced, along with the other plans the Mayor introduced at Internet Week. And, digging deeper into her team, we get past the press releases and into some uncharted territory for most City Hall employees. "We're focused on a New Yorker's user experience with the government. We're going to try to create nimble ad hoc project teams and push things over the goal line that way." Like what? "There are lots of opportunities for New York to be on the cutting edge of making life easier for small business entrepreneurs [online]. There are a lot of different regulations in different cities to bringing your product to market but if a maker really wants to touch all markets and be competitive in New York, they have to be in compliance with those product standards. There's no centralized way for somebody who wants to sell something in both Los Angeles and New York to compare the regulations—to juxtapose all things and come up with a baseline. So the idea is we'd do something open source and put it up on GitHub and try to get other cities to build off of that too and have some sort of municipal open source system to help entrepreneurs."

Jessica is still building out her team, and she has just learned where all the bathrooms are, she says, so projects like these may not be around the corner, but the spirit of innovation is there, threatening to prove so many of us nail-biters wrong.

When I finally ask Singleton about being at the apex of politics and tech—two heavily male-dominated fields—she credits her success to the mentors she has had along the way but also advises, "Do good work, defend your work, and elbows out when you need 'em." I pity anyone on the end of the latter.